Orpheus' Oath
by ApatheticOnion
Summary: Sam goes to Hell to rescue Bobby, only to be confronted with a choice he never imagined he would have to make. Sam/Jess, some hinted Destiel.
1. Chapter 1

She wasn't supposed to be there.

They had it planned out. Get in, save Bobby, get out. There was never meant to be a choice. It wasn't supposed to be this hard.

It wasn't supposed to be this hard.

Bobby was the first person he'd seen when he got to Hell. Standing at the window, gazing up through the bars without a scratch on him. Just the same old Bobby, baseball cap and attitude and all, looking for all the world as if he'd just been out of town for a while, no biggie, he was back now and everything would be okay. All Sam had to do was grab him and go.

But then he saw her. Scared, curled into the corner in the shadows and barely recognizable from the burns that covered her once near flawless skin, hair more bloody and burnt than blonde framing her skeletal face, but those familiar blue eyes staring at him, pleading with him.

Jess.

Sam couldn't speak as he stared at her. Couldn't believe she was there, didn't want to admit he had abandoned her to hundreds - thousands? - or years of torment.

"Jess?" Sam whispered, his voice choked. Bobby still stood at the window, gazing up at the false sky. He hadn't noticed Sam.

"Sam-" Jess released an ear-splitting scream as her body burst into flames, the smell of burning flesh filling the room and making Sam choke. The flames died down as quickly as they appeared, leaving Jess sobbing quietly in the corner as Sam stared.

"Jess, I'm so sorry-" Sam started towards her, but stopped as smoke began to curl upwards from her form once again. Jess whimpered as he held one hand out towards her, wanting so desperately to touch her, to comfort her, to tell her everything would be okay-

"Hello, moose."

Sam spun around at the sound of Crowley's voice, knife drawn in defense. Crowley scoffed.

"Down, boy. I just want to talk." Crowley flashed his most reassuring smile, like a serpent who has finally managed to corner it's prey but isn't quite hungry enough for the killing strike. "I see you found our guest of honor."

Jess burst into flames once more as Crowley smiled serenely. This time it was Sam who screamed loudest, flying instinctively to her side, but she disappeared the moment his hand touched hers. Crying, she reappeared on the other side of the room, Crowley between her and Sam.

"Let her go." Sam growled, knuckles white on the knife handle. Crowley grinned.

"And if I say 'no'?"

Blindly, Sam lunged. The knife flew from his hand and into Crowley's.

"Now, now. Didn't I say I just wanted to talk?"

Chest heaving with anger, Sam could do nothing but glare past Crowley, eyes locked on Jess's as she fell into silence once again. Her eyes had melted.

"Let her go." Crowley laughed at Sam's demand, tossing the knife carelessly into the air before catching it again.

"And why would I do that, hm? Let you go about closing the gates of Hell? Bad for my business you know. Oh yes, I've figured it out." Crowley smirked as he fingered the knife blade, relishing the shock on Crowley's face. "That taxi driver was quite eager to share his information with me. Pity I had to kill him."

Sam felt a momentary pang of guilt and panic for the taxi driver, but pushed it aside.

"She doesn't belong here, she doesn't-" Sam stopped, taking a deep breath and looking Crowley dead in the eye. "She doesn't deserve this."

"Well, perhaps she should have chosen her boyfriends more wisely, eh, Winchester? But don't worry, I'm a reasonable man. No, really." He added, hearing Sam's audible scoff. "I've always been a sucker for making deals."

Sam frowned as Crowley began slowly circling around him like a vulture.

"What kind of deal?" Crowley grinned, handing the knife back to Sam, who pocketed it uncertainly.

"A trial, of sorts." Sam cringed at the wording, but said nothing, listening intently now. "You take Jess - I keep Bobby, of course, let's not get greedy - and you both walk out of here, no harm, no foul. BUT-" Crowley paused, smile gone as he folded his arms behind him, all business now. "You cannot touch look at her until you're out of Hell and purgatory."

Sam stared at Crowley, then glanced at Jess. It only took him a moment to decide.

"Deal."

Crowley grinned and grabbed Sam's hand in a firm shake. A sharp pang shot up his arm, seeming to settle in his chest... around his heart.

"What did you do?" Sam choked against the sudden pain. Crowley smiled.

"Ah, yes. One last bit, forgot to mention. Your heart may explode before you get back." Sam lunged at him once again, but was left grasping only air as the sound of Crowley's laughter rang in his ears. He turned towards the door, eyes squeezed shut. He could already feel pressure beginning to build in his chest.

"Jess?" He said quietly. A soft shuffle resounded from behind him, like one struggling for purchase against the ground. Sam dug his nails into his palms to keep from turning around.

"Are you okay?" Such a stupid question.

"Yes." Came the soft reply. Sam choked back tears as he nodded, as much to himself as to Jess.

"Let's go."

Sam led the way slowly, carefully out of the room and down the hall, paying one last glance to Bobby before exiting the room. Bobby would be okay. They would find another way to get him out. Dean would understand. Wouldn't he?

Sam shook the thought from his mind as he continued walking, encountering no demons, no obstacles; just the slowly building pressure in his chest. Behind him came the soft sound of shuffling footsteps and occasional gasps of pain that tore into Sam like a knife. As they reached the door to Purgatory, Sam stopped. what if they were attacked?

"Jess, I need.. I need you to listen to me." Silence behind him. Sam started to turn, but was stopped by a soft cry of panic from Jess.

"I know, I can't turn around. I'm sorry." Sam felt tears start to trail slowly down his cheeks, and he hastily wiped them away. "We're going somewhere dangerous - it's the only way to get back to the real world. If anything attacks us, I won't be able to..." Sam choked, taking a deep breath to calm himself. "I won't be able to help you, Jess."

There was silence again, and for a moment Sam had a horrible feeling that Jess was simply standing there, hating him for all he had done to her.

"I trust you." Jess whispered, and Sam nearly spun around then and there to embrace her. Instead, he released a sob-choked laugh and pushed open the door.


	2. Chapter 2

Dean swore as he slammed the door to the taxi closed. That man had been his only hope of retrieving Sam and Bobby from Purgatory. What the hell was he going to do now?

Dean leaned up against the side of the cab, putting his hands over his face before running them both backwards through his hair and bringing them to rest at the back of his head as he stared up at the sky in desperation. Cas was out of the question; if he'd been able to get in and out of Purgatory, he would have done so on his own ages ago and spared them the year in Monster's Paradise. There was only one other person who had ever gotten out…

Dean shook his head, forcing away the thought of Benny. He already owed the vampire so much, he couldn't ask him to do what he needed to get Sam. If that would even work... Dean shoved his hands in his pockets, finger finding his cellphone and wrapping around it instinctively as he sighed, rubbing at his face with one hand again before flipping the phone open and pushing the speed dial. Maybe Benny would have another idea.

He had to try.

Sam grunted as he forced the large stone back over the entrance to Hell, careful not to get sucked back down through the portal. The stone fell into place with a clunk and an ominous sort of hiss against the vacuum of the portal, then there was silence. Sam started to turn, but stopped, remembering who was behind him.

"Jess? You still there?"

"I'm here, Sam." A wave of relief washed over Sam at the sound of Jess voice coming from the riverside. She sounded stronger now. The pain in Sam's chest doubled.

"We have to follow the river back up about three miles, that way." Sam pointed out ahead of him and down the river, where the taxi driver would be waiting. "We have about an hour until the guy is supposed to meet us to get us out. Can you make it?"

There was a moment of silence, then a small laugh. "Yes. Sorry, I just realized I was nodding my head. I guess you couldn't see that, could you?"

A squeeze of pain that had nothing to do with Crowley's curse ran through Sam's chest as he smiled sadly.

"Soon, Jess. I promise." He heard Jess approach him, and felt something sharp poke at his hand. Glancing down, he realized the end of a long stick had been prodded into his hand.

"Here, it's almost like holding hands." Sam laughed, giving his end of the stick a small shake in response and hearing Jess laugh in return. "Let's go."

The woods of Purgatory were quiet as they made their way along the river. Every so often they would exchange small talk – how had Sam been, did he ever graduate from Stanford, was his brother still driving that old car of their dad's? Jess' voice grew stronger as they walked; by the time they had gotten halfway to the meeting point, she sounded almost back to normal. Sam was starting to have trouble disguising the pain around his chest now.

"Sam?" Sam snapped back to reality as Jess' voice invaded his attempts to mentally quash down the building pressure in his chest. He realized Jess had asked him a question.

"Sorry, what was that?" Sam kicked himself as he realized just how short of breath he sounded, and was sure Jess had caught the hitch in his voice as well. There was quiet for a moment.

"I'm sorry about this." Jess whispered. Sam stopped, confused.

"What? What do you have to be sorry for?" Sam asked, inclining his head backwards as if he might look at her. He could hear Jess fidget.

"If I'd never let Brady in that night… Sam, this is all my fault." For a moment Sam thought his heart had burst as he spun around to face Jess, eyes squeezed shut at the last moment.

"Don't you _ever_ say that, Jessica." Sam snapped. His head was spinning. "None of this was your fault. _Ever_."

"Sam…" Jess' voice was low, sad. Sam had to turn back around to keep himself from looking at her. He waved his end of the stick in his hand to remind Jess to grab back onto it; she had released it when he turned around. "I love you."

Sam felt tears sting his eyes as he gripped the stick between them so hard he feared it might snap. "I love you too, Jess."

"Benny." Dean embraced the vampire with a grin as Benny smirked, swinging an arm around to clap Dean on the back.

"Hey there, friend." They pulled apart, Dean's eyes on Benny as he looked over the alleyway. "So, this is it, huh? Gates to Purgatory?"

"I guess so. This is where the guy disappeared with Sam, anyway." Benny leaned around Dean to look into the cab; the front seat was empty.

"I took care of it." Dean added. Benny nodded. "Any ideas how to spring Sammy back out again?"

"What about that angel friend of yours?" Benny asked, shooting a backward glance at Dean as he examined the walls of the alley. "How'd he get out?"

"Some feathers on a power trip up in Heaven, from what I've heard. Name's Naomi. You ever heard of her?" Benny shook his head, knocking his knuckles against the alley wall in defeat before turning back to face Dean.

"Well, it looks to me like we've got only one option." Benny offered, leaning against the taxi. "I don't suppose you've got any weapons I could sneak over there with me, huh?"

Benny's smirk slid off his face as he caught sight of the pain in Dean's face. He straightened up, clapping one hand on Dean's shoulder as he looked him straight in the eyes.

"He's family, Dean. I get it. I'd do the same thing in your position." Sam didn't look convinced. There was a tense silence as Dean just stared at him, usual snark and carefree remarks abandoning him for the moment. Benny patted Dean's shoulder, moving to stand in the middle of the alley.

"You ready?" Dean nodded, retrieving a machete he had stashed in the back of the cab. Slowly he unsheathed it, moving it from hand to hand with growing reluctance as he looked up at Benny once again.

"Thank you." Dean whispered. Benny smiled as best he could.

"Don't worry about it, Dean. I don't much belong around here anyway. I could use a vacation." Dean almost laughed.

"Like Hell you do. The moment you find Sam, you hitch a ride straight back here, fare's on him. You got it?" Benny grinned.

"I got it, friend. Now…" Benny gave himself a light shake, arms held slightly out from his side as he smiled at Dean. "I'm not getting any younger here." Dean nodded, eyes watering as he raised the machete.

"Thank you."

Dean swung.

Sam stopped as they reached the appointed meeting spot. Glancing at his watch, he sighed, rubbing at the pressure now causing black spots to dance before his eyes. Behind him, Jess lightly shook her end of the stick to get his attention.

"Sammy?" Jess whispered, fear evident in her voice. Sam straightened as best he could.

"This is the spot." Sam mumbled, looking around the clearing for any sign of the cab driver. Nothing.

"Maybe he's just… running late?" Jess sounded so hopeful Sam wanted to cry.

"I don't think so." Sammy let out a cry as his knees suddenly buckled, one hand scraping against the forest debris as his other grabbed desperately at the pain in his chest. His head collided with the forest floor and left him seeing stars.

"Sam!" He could feel Jess drop to her knees beside him, practically feel her struggle not to touch him. He rolled away slightly to try and keep her from doing so.

"It's okay. He'll be here soon…" Sam gasped, eyes clenched shut against the pain. Everything hurt…

A sudden snap resounded from somewhere to Sam's left and he froze. Beside his he could sense Jess had done the same. "Jess?"

"Someone's coming." Jess whispered. Sam grunted, attempting to sit up. "Don't, Sam!"

"I have to see who it is," Sam gasped, struggling to his feet. "Move back so I don't touch you."

Sam heard Jess stumble away behind him, and he opened his eyes as a familiar figure appeared through the dead trees. Sam blinked, not believing what he was seeing.

"Benny?" Sam mumbled, blinking once more as he stared in confusion at the approaching vampire. Benny grinned in response.

"Hey there, Sam. Your brother sent me to get you." Sam stared at him, realization dawning on his face as the gravity of Benny's situation sunk in. Benny's grin faltered slightly for a moment as he made eye contact with Sam, but it was quickly replaced with surprise as he turned and caught sight of Jess.

"Who might this be?" Benny asked, inclining a head towards her. Sam heard Jess shift slightly behind him.

"This is Jessica. My girlfriend." Sam caught the brief look of horror that flashed across Benny's face as the full force of Sam's statement apparently hit home. Benny moved forward, past Sam, one hand extended.

"It's a pleasure to meet you, ma'am." Sam caught a glimpse of Benny bending over in a light bow, apparently to kiss Jess' hand judging from the light laugh that followed.

"I like this guy, Sam. Where've you been hiding him?" Jess teased. Sam grunted an attempt at a laugh in reply.

"Oh, you know. Purgatory."

"Alright you, let's get going before your brother takes my head off." Sam groaned in equal parts pain and unamusement as Benny took the lead. He suddenly stopped, catching sight of Sam's hand still clutched at the fabric over his heart. "What's wrong?"

"Crowley." Sam managed, stumbling slightly as he began to sway. Benny darted forward in time to catch Sam as his legs buckled once more, a soft gasp eliciting from Jess behind him. Benny wrapped Sam's arm over his shoulder and gripped Sam around the waist.

"Little lady, if you wouldn't mind taking his other side-"

"NO!" Sam yelled, nearly winding himself. Benny looked at him in alarm. "Can't touch her." Sam gasped, coughing. "Part of the deal. Can't see her, either." Benny's mouth set in a grim line.

"Well, then. The sooner we get you two out of here, the better. Come on." Sam grunted as Benny forced them forward, Jess' footfalls sounding quietly on the underbrush behind them.

"Where are you taking us?" Jess asked after a few mins. Benny glanced back at her from his vigil of the surrounding forest, readjusting his grip on the barely-conscious Sam at his side.

"There's a portal a little ways ahead." Benny gestured to the woods in front of them. "We should be nearly there."

A snap and the sound of voices laughing made Benny freeze in his tracks. Benny turned, his face grim.

"Jessica, was it?" Sam tried to force his eyes to focus on whatever it was Benny was looking at, but he could barely turn his head. "I'm going to have to ask you to run."

"Sam." Sam moaned as Benny grabbed Sam by both shoulders and forced him to look at him. "you're going to have to make it to the portal on your own. I'll hold them off as long as possible." Sam attempted to mumble a protest in response, but Benny shushed him. He reached over to one of the trees nearest them, tearing off a sizeable lower branch as if it were no more than paper. He thrust it into Sam's hands like a walking stick.

"_Go_." Sam stumbled as his full weight dropped onto the branch in his hands, Benny releasing an animal-like snarl as he took off behind him. Sam took a shaky step forward as he heard Jess come up behind him.

"Come on, Sam." Jess whispered. Sam grunted, pain shooting through his chest as he took another step forward.

"Go, Jess. Hurry." Sam heaved himself forward again, air ripping from his lungs as pain like fire seared through his heart.

"I'm not leaving you." Jess snapped. Sam forced himself forward again. The sound of snarls and screams could be heard behind them now. They were running out of time.

"I see it, Sam!" Why did Jess sound so far away? Sam's head spun as his grip on the branch loosened. "Sam!"

Sam vaguely registered that something horrible had happened as a hand gripped his arm tight and hauled him forward. An arm wrapped itself around his waist as he was heaved forward, a dazzling blue glow now shining too brightly into his eyes. Sam moaned, his head swimming as his heart began to pound faster and faster within his chest.

"Almost there, Sam." Whose voice was that? Jess – why did she sound so close-

"No," Sam gasped, glancing to his side and catching sight of Jessica, arm wrapped around his side as her other hand held his over her own shoulders, supporting him as best she could. "Jess, you can't-"

"Too late, Sam." The smell of burning flesh filled Sam's nostrils as Jess heaved him up towards the portal. Sam could see the flesh on her face already beginning to peel.

"Jess." Tears flowed freely down Sam's cheeks as their eyes met. Jess was dissolving before his eyes.

"I love you, Sam." Jess whispered. She pressed her cracking lips to his, then shoved him into the portal. The last thing Sam registered was a pair of bright blue eyes disappearing into a cloud of smoke.

"JESSICA!"


	3. Chapter 3

Sam hit the ground hard as the world around him spun out of focus. The first thing he was aware of was that the pressure in his chest had completely stopped. The second was that he wasn't alone.

"Sammy!" Sam groaned as Dean grabbed him roughly by the arm, hauling him to his feet and embracing him in a rib-crunching hug. Sam stumbled as Dean released him, grabbing Sam by the wrist and pulling on his sleeve.

"Dean- no-" Sam choked, still fighting to stop the reeling in his head. Dean yanked Sam's sleeve up to reveal his forearm, already reaching for his knife with the other.

"Come on, Sam, let's get this trial over wi-" Dean froze as he looked in confusion at the bare flesh of Sam's arm. He immediately grabbed onto Sam's other arm, hauling up the sleeve in wild hope, only to stare at it blankly for several long moments before slowly raising his head to meet Sam's gaze.

"What happened, Sam?"

Sam opened his mouth to answer, but found his throat was too constricted. Dean's face lit up in alarm as Sam began to openly sob, dropping to his knees in the dirt once more.

"Sammy- Sammy, it's okay, it's okay-" Dean knelt in the dirt beside Sam, arms wrapped protectively around him as he unconsciously began to rock Sam gently from side to side the way their mother had done for Dean when he was a child. Sam sobbed for several long minutes, not caring that his big brother had gone into full-blown parent mode. He imagined they must look fairly odd, two grown men sitting out in the middle of a forest in the middle of the night, rocking each other- okay, that was enough.

Sam pulled away, rubbing at the tear streaks on his dirty face as Dean moved back to give him space, face still taught with worry as he watched his younger brother. For the first time, Sam realized just how many lines now covered Dean's face from the years of worry and stress he'd gone through. He briefly wondered how much his own must have changed, but pushed the thought aside.

"I found Bobby." Sam managed at last, coughing the remainder of his sobs from his throat. "But he wasn't alone. Jessica was there, too." Dean frowned in response.

"What the hell was she doing there?" Sam shook his head.

"I don't know. But she… she'd been…" Sam's voice trailed off. Dean nodded that he understood. Sam took a deep breath.

"Crowley came. He said he'd make a deal with me – if I could get both Jess and myself out without seeing or touching her, he'd let us go. He didn't tell me until after we made the deal that my heart was also going to explode if we took too long."

"Son of a bitch." Dean sat back, running a hand through his hair. Sam snorted.

"We got to the clearing without a problem. That's… we found Benny." Sam watched Dean's face for a reaction. Dean avoided his gaze, frowning down at the ground as he listened.

"He got us to almost to the portal, but we were attacked. He made us go on ahead." Sam saw a nerve in Dean's face twitch, causing the rest of his sentence to flow out in a rush. "I'm sorry, Dean, I could barely walk at that point, I should have argued with him, made him stay-"

"He wouldn't have, Sam." Dean mumbled. He glanced at Sam, and seeing the guilt on his face, his own expression softened. "I know the bastard, Sammy. He never runs from a fight."

"No wonder you two got along so well." Dean chuckled, picking up a rock and fidgeting with it in his hands as he stood and began to pace.

"So what happened?" Sam blinked, pinching at the bridge of his nose.

"Jess grabbed me, she got us to the portal." Sam felt tears beginning to sting his eyes again. "She broke the deal, Dean. She's gone." The two lapsed into a heavy silence as Sam stared down at his hands. He realized there was a faint scorch mark where Jess had been holding onto it as she hauled him to the portal. "I let her down again."

"No." Sam started as Dean grabbed him by both shoulders, forcing him to his feet to meet his gaze.

"You did everything you could, Sam. This isn't your fault. Got it?" Sam was almost taken aback at the sincerity in his brother's face. He nodded. Dean released him, sighing.

"So now what do we do? Start over, try again next week?" Sam shook his head.

"I don't know. Does failing a trial mean you have to start all over?" Dean swore, kicking at the underbrush. "Maybe we could-" Sam stopped, realizing Dean was no longer paying attention to him. "Dean?"

"Cas." Sam opened his mouth in confusion, only to have Dean push past him. Sam turned, startled to see that Castiel had in fact appeared behind him. Dean stopped just short of Castiel, apparently internally struggling with a desire to either hug or punch the angel. Sam was never really sure which, lately.

"Hello, Dean. Sam." Castiel nodded to Sam, who managed an awkward half-wave in return. "I need both of you to come with me."

"Why, what's-" Dean yelped as Castiel suddenly grabbed onto both him and Sam, and the world spun mercilessly around them, sending Sam's head to pounding once more. The ground suddenly returned beneath them, and Sam stumbled sideways. Dean caught him by the shoulders, steadying him as they both looked around in surprise.

"Cas, not for nothing, but you wanna tell me why you brought us to Hell?" Dean's voice rose towards the end, Sam gazing around in alarm at the thought that Castiel might have gone crazy again. His eyes widened in shock as they fell on a figure tied to a chair in the center of the room.

"Now look, boys, we can all be civil about this-" Crowley hissed through gritted teeth, struggling against the bonds on his chair. A demon trap on the floor held him in place. "This really isn't necessary."

"You have two souls in your possession that are rightfully Heaven's." Castiel interrupted. Crowley stopped struggling to eye Castiel with obvious distaste.

"Yes, well. Mix ups happen, I'm sure you understand." He subconsciously cringed away as Castiel came to stand at his elbow, demon blade drawn. "Of course, I'd be willing to work out an agreement."

"Where's Jessica?" Crowley took his gaze off of Castiel long enough to shoot a smug grin at Sam.

"What's wrong, Moose, didn't make it home?" Crowley yelled in pain as Castiel jabbed him in the shoulder with the demon blade, eliciting a slow stream of smoke. "Alright, alright! You can have her!"

There was a flash, and Jessica appeared on the floor, skin bubbled and cracked from the flames of her torture. Sam rushed to her side, wrapping his arms gently around her as he cradled her in his arms. She looked blearily up at him in confusion, a small light of hope in her eyes. "Sam?"

"Jess." Sam laughed, hugging her close to him. He felt a shuddering sensation under his hands and realized her skin was repairing itself. Within moments, she was back to normal. Sam kissed her."

"Not that this isn't touching, really," Crowley interjected, grimacing at the happy couple on the floor. "But could you possibly untie me now? It doesn't exactly inspire confidence in the troops to see their leader held at bay by two humans and a glorified pigeon in his own domain."

"I dunno, Cas, I think we should leave him here." Dean smirked, circling around Crowley to join Castiel as Sam and Jessica got to their feet. "Maybe he'll think twice about backstabbing us again in the future."

"I don't recall Crowley ever sticking a knife into your back, Dean. When was this?" Castiel frowned in concern, raising the demon knife once again to Crowley's immense discomfort.

"It's just a phrase, you idiot-" Crowley yelped in pain as Dean 'accidentally' brushed Castiel's hand, causing the knife to jab Crowley's right ear.

"I believe you still owe us another soul." Castiel glanced at the door to the cell they stood in, where muffled attempts to open the door could be heard. Crowley caught his discomfort and smirked.

"What's the matter, angel, don't fancy a fight today? Did you just have your wings drycleaned?"

"My wings are incorporeal and do not require cleaning. Where is the soul of Bobby Singer?"

Another flash of light, and Bobby stood in the center of the room, blinking in confusion.

"What the blazes is going on here?" Bobby yelped, taking in the sight before him. "I know you boys had gotten into some crazy lately, but this is going a little overboard, don't you think?"

"Now, that's all settled, will someone please UNTIE ME?" Crowley howled. A particularly loud thump on the door to the cell made everyone jump. Castiel moved to Sam's side and gripped his arm, slicing it open.

"What are you-" Castiel mumbled a strange series of words as the door the cell began to crack. Jessica's body began to glow, then flowed into the cut Castiel had created on Sam's arm, sealing the wound.

"Bobby." Dean pulled out his own knife, slicing across his own forearm and muttering the same words as Bobby glowed and then disappeared inside his arm. Dean nodded to Castiel, who still had a hand on Sam, and Castiel gripped Dean's shoulder. A flash of light later and Team Free Will had gone, the door to the cell crashing inwards as the angel's power left the realm. A small host of demons stood in the entrance, gawking at their Lord still bound to his chair over a demon sigil. Crowley glared at them.

"Take your time, boys. No hurry."

For the fourth time that day, Sam found himself spinning through time and space. This time, however, Castiel was kind enough to make sure he didn't topple over upon regaining his footing. Sam moved away from Castiel the moment they landed, apparently back in the forest in Maine, and pulled up his sleeve to see the soft glow of Jessica's soul still burning brightly beneath his skin. He smiled.

"Cas, how did you know…" Dean trailed off, staring at Castiel in amazement. Castiel pointedly avoided Dean's gaze.

"Just because I don't always answer you doesn't mean I don't hear your prayers, Dean. I thought we had established this by now." Sam looked away, feeling slightly embarrassed for his brother. Dean continued to stare at Castiel in confusion.

"But- Crowley- how the Hell did you manage that?" Dean gestured towards where Crowley had been seated moments before.

"I have my connections. Martha Stewart still owed me a favor." Dean stared at Castiel blanky as the angel moved towards Sam, his knife extended handle first. "You'll need this."

Sam looked at it in confusion for a moment before taking the knife into his own hand. He held the gleaming blade over the place where Jessica's soul was nestled safely under his own skin, then carefully sliced back across the flesh to release her. Her soul sat unmoving for a moment, as it unwilling to leave Sam, then slowly flowed out into the night sky, hovering warmly a few feet over Sam's head. Sam felt a warm wind brush his face, and almost thought he heard the words 'thank you' on the wind before her soul swirled and flew up towards the Heavens. Sam realized tears had begun to trickle down his cheeks again, but this time, he didn't brush them away. He stood there, smiling at the sky as Castiel moved back to Dean, who had pulled out his own knife and was now releasing the soul of Bobby into the clearing. It glowed a faint blue and flowed loosely about Dean's shoulders for a moment, as if it were attempting to hug him, then flew off and up after Jessica's soul. The three of them were left standing in silence for several moments before Castiel lowered his gaze and began to move off towards the edge of the treeline.

"Cas!" Castiel stopped, turning to face Dean, but not quite looking at him. Sam thought he could see a trace of shame on his face. Dean made a strange gesture with his arm, as if he wanted to reach for Castiel but thought better of it. "Thank you." Castiel nodded, and, for a brief moment, Sam thought he saw him give Dean a look of... what, gratitude? No, it was stronger than that- but then he was gone, and Sam pushed the thought away, retreating to his brother's side.

"You okay, Sam?" Sam nodded. Dean sheathed his hunting knife, tucking it away in one of the inside pockets of his coat. "Hell of a night, huh?"

"Yeah, can you… can you do me a favor and not use that phrase for the next… ever?" Dean chuckled, straightening his jacket.

"Fair enough."

The two of them made their way out of the woods in silence, Sam's gaze largely fixed on the sky. When they reached the impala, he realized he was still smiling again.

"Hey, Dean?" Dean opened his door and stopped, looking at Sam. "Castiel said Crowley only had two souls of Heaven's. Do you think Adam-?" Sam lowered his gaze from the sky to look at Dean, who was frowning down at his hands.

"I don't know, Sam. But we'll find out." Dean slid into his seat and started the car, as Sam slunk into the passenger side.

"One more thing." Sam pointedly avoided looking at Dean's face as he buckled his seatbelt, fighting back a smirk. "You and Cas, are you like... a thing now?" Dean deadpanned, pulling his hunting knife from his pocket and pointedly placing on the dashboard between them.

"Shut up, Moose."


End file.
